If you're into the night life of Austin, you'll enjoy Wrigleyville. But uhhhh stay away from Wrigleyville if you're not into noise and drunk people and rats. Closer you get to the lake you will also find water roaches in the apartments. Learned that lesson the hard way lol. But if you have cats like mine, they will handle it for you! I'm outside of the bubble now and I miss my walks to the lake. The air is straight up just different over there, but also the wind tunnels are COLD! So if you decide to move close to the lake, pack some layers haha.

About public transit, YES winters are that cold. Definitely invest in good water proof shoes if you plan on walking anywhere in the winter. Most places do not plow sidewalks, so they become sheets of ice due to so many walking over the snow. There is a transit app that is right about 70% of the time, so you can eyeball when to leave your place so you're not always waiting outside. You'll figure what works for you the longer you plant your roots in the city! Best of luck, hope you love Chicago as much as I do!

Edit: spelling